2-Aminobenzophenone, condensation with

Reaction of 2-aminobenzophenone with acetyl acetone in the presence of Bi(OTf)3 (5 mol%) results in the formation of 3-acetyl-2-methyl-4-phenylquinoline [117]. Various 1,3-diketones, acyclic ketones and cyclic ketone undergo the condensation with 2-aminoaryl ketones. The scope and generality of this process is illustrated with respect to various 2-aminoaryl ketones and a wide array of a-methylene ketones, and the results are summarized in Table 6. This method is free from side reactions such as the self-condensation of ketones, which is normally observed under basic conditions. Unlike reported methods, the present protocol does not require high temperature or drastic conditions to produce quinoline derivatives. 

Aldehydes have also been condensed with 2-aminobenzophenone oximes 811, but in this case an added oxidant is not needed, as loss of water from the iV-oxide intermediate 812 provides 2-substituted -phenylquinazolines 813 directly <2004AP239>. 

Tetrazolylquinoline 156 was obtained in three steps involving an acid-catalyzed condensation of aminobenzophenone 153 with 3, 3-dimethoxypropionitrile 154 followed by classical tetrazole chemistry (Scheme 29) (04JME2574). 

The phthalide 25, obtainable by condensation of 4,4 -bisdimethyl-aminobenzophenone-2-carboxylic acid with 3-dimethylaminoacetanilide and subsequent hydrolysis, was diazotized in sulfuric acid and the resultant diazonium salt treated with copper powder to yield 26. However, better yields are reportedly obtained by carrying out ring closure of the diazonium salt in phosphoric acid.103 A further synthetic route has also been described in which phthalides undergo intramolecular cyclization in the presence of aluminum chloride and urea.104,105 Thus, Crystal Violet lactone (2) has been directly converted into phthalide 26.106... 

Condensation of an aminoketone with urea leads to the formation of a quinazolone by incorporation of carbonyl carbon and one amino group. Thus reaction of the aminobenzophenone (84-1) with urea can be rationalized by assuming the initial formation of the urea exchange intermediate (84-2). Cyclization will then give fluproquazone (84-3) [94], a nonopioid analgesic that shows NSAID-like activity in the absence of a typical acidic function. 

Pigment Blue 1 [1325-87-7] 42595 2 triarylcarbonium PTMA salt (Victoria Blue B) condensation of 4,4 -bis-IV,IV-dimethyl aminobenzophenone with N-ethyl-l-naphthyl amine, followed by oxidation and salt formation... 

An alternate synthetic strategy for benzodiazepines involves the condensation of resin-bound a-amino esters 17 with 2-aminobenzophenone imines followed by TFA treatment of the intermediate to effect cleavage and cyclization [27], The parallel synthesis of 40 discrete benzodiazepine analogs 18 was performed, and expected SAR data were generated in a bioassay based on the inhibition of fluoronitrazepam (Fig. 4). 

Beier and Pastyrikova (13MI411) reported that reductive ring opening of SFs-substituted benzisoxazoles 78a, 79a using iron in aqueous AcOH resulted in excellent yields of ori/ o-aminobenzophenones 100, 101, which can be used as precursors for the synthesis of other SFs-substituted heterocycles such as quinazoHnes (see Section 2.8), as weU as for the synthesis of SFs-substituted quinolines. Thus 6-SFs-quinoline 102 was prepared in high yield by the Friedlander annulation reaction of 101 with excess ethyl acetoacetate in the presence of catalytic cerium (IV) ammonium nitrate (CAN). Similarly, aminoketone 100 was condensed in good yield with cyclohexanone to provide 7-SFs-quinoline 103 (Scheme 25). 

The authors successfully prepared chemically cross-linked temperature-responsive electrospun nanofibers by thermal curing [llj. As a member of the NIPAAm family, N-hydroxymethylacrylamide (HMAAm) was copolymerized with NIPAAm by free-radical copolymerization because temperature-responsive HMAAm can be cross-linked by self-condensation at high temperatures (above 110°C). As a result of cross-linking, very stable nanofibers in aqueous solution were obtained and manipulated as a bulk material. By extension of the above-mentioned examples, the authors successfully prepared temperature-responsive electrospun nanofibers by photocuring [12]. The temperature-responsive nanofiber mats were prepared using the copolymers NIPAAm and 2-carboxyisopropylacrylamide conjugated to 4-aminobenzophenone, a photoinitiator. The crosslinked temperature-responsive nanofibers were obtained by UV irradiation for 30 min (Fig. 5.4.3). Chemically cross-linked nanofibers were also reported by... 

The third route permitted a direct access to acronycine (2), by cyclization of the aminobenzophenone 352, efficiently prepared by condensing JV-methylisatoic anhydride (259) with the lithiated chromene 360, Treatment of 352 with sodium hydride in dimethylsulfoxide gave acronycine (2) and isoacronycine (335), both obtained in 38% yield. 

The ( )- and (Z)-configurations of compounds (15 R = H, Me, or Ph Ar = Ph, 2-furyl, 2-thienyl, etc.) have been prepared by condensation of 2-hydrazinobenzothiazole with o-aminobenzophenones, or the appropriate heterocyclic aldehydes or ketones, the isomers then being separated. Their... 

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